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Fischer esterification is an acyl substitution reaction based on the electrophilicity of the carbonyl carbon and the nucleophilicity of an alcohol. Carboxylic acids tend to be deprotonated by nucleophiles, which gives an unreactive carboxylate.
Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
Upon treatment with strong acids, alcohols undergo the E1 elimination reaction to produce alkenes. The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols are eliminated easily at just above room temperature, but primary alcohols require a higher ...
Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. [1] Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile.
The Williamson reaction is also frequently used to prepare an ether indirectly from two alcohols. One of the alcohols is first converted to a leaving group (usually tosylate), then the two are reacted together. The alkoxide (or aryloxide) may be primary and secondary. Tertiary alkoxides tend to give elimination reaction because of steric hindrance.
An example of a solvolysis reaction is the reaction of a triglyceride with a simple alcohol such as methanol or ethanol to give the methyl or ethyl esters of the fatty acid, as well as glycerol. This reaction is more commonly known as a transesterification reaction due to the exchange of the alcohol fragments. [2]
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid.